Tag: M.W=50-100

Jiang, Ji published the artcileDiscovery of hydroxyl 1,2-diphenylethanamine analogs as potent cholesterol ester transfer protein inhibitors, Recommanded Product: (R)-Oxiran-2-ylmethanol, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(14), 3278-3281, database is CAplus and MEDLINE.

Hydroxyl 1,2-diphenylethanamine analogs were identified as potent inhibitors of cholesterol ester transfer protein (CETP), a therapeutic target to raise HDL cholesterol. In an effort to improve the pharmaceutical properties in the previously disclosed DiPhenylPyridineEthanamine (DPPE) series, polar groups were introduced to the N-linked quaternary center. Optimization of analogs for potency, in vitro liability profile and efficacy led to identification of lead compound 16 which demonstrated robust pharmacodynamic effects in human CETP/apo-B100 dual transgenic mice.

Bioorganic & Medicinal Chemistry Letters published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Recommanded Product: (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kadirvel, Manikandan published the artcileInhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; a novel potent inhibitor of AI-2 signalling, Product Details of C3H6O2, the publication is Chemical Communications (Cambridge, United Kingdom) (2014), 50(39), 5000-5002, database is CAplus and MEDLINE.

(S)-4,5-Dihydroxypentane-2,3-dione [(S)-DPD] is a precursor for AI-2, a quorum sensing signalling mol. for inter- and intra-species bacterial communication. The synthesis of its fluoro-analog, 4-fluoro-5-hydroxypentane-2,3-dione (4-fluoro-DPD) is reported. An intermediate in this route also enables a new, shorter synthesis of the native (S)-DPD. 4-Fluoro-DPD completely inhibited bioluminescence and bacterial growth of Vibrio harveyi BB170 strain at 12.5 μM and 100 μM, resp.

Chemical Communications (Cambridge, United Kingdom) published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Product Details of C3H6O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Finkel’shtein, E. Sh. published the artcileElectrophilic addition to methylenecyclobutane and bicyclobutylidene, HPLC of Formula: 20117-47-9, the publication is Neftekhimiya (1985), 25(1), 48-57, database is CAplus.

Title reaction of methylenecyclobutane (I) with ROH (R = Me, Et, Bu, 1-methylcyclobutyl, Ph, Ac, ClCH₂CO, FCH₂CO, CCl₃CO, CF₃CO) in the presence or absence of hexane or cyclohexane and/or 80% H₂SO₄ gave the corresponding ethers and esters II. PhOH gave 4-R¹C₆H₄OH (R¹ = 1-methylcyclobutyl) and 2,4,6-R¹₃C₆H₂OH (same R¹) as the major products. Analogous reactions of bicyclobutylidene with ROH (R = H, Me, Ac, CF₃CO, Ph) gave bicyclo[3.3.0]octanes III (R² = OH, OMe, OAc, O₂CCF₃, C₆H₄OH-4, resp.). I reacted with aqueous HCHO under these conditions to give 5,7-dioxaspiro[3.5]nonane, methanolysis which gave diol IV (R = H) (V) and IV (R = Me). Dehydrating V gave 1-vinylcyclobutene . The NMR and mass spectra of the products were interpreted.

Neftekhimiya published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, HPLC of Formula: 20117-47-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ilic, Milos published the artcileTowards dual antithrombotic compounds – Balancing thrombin inhibitory and fibrinogen GPIIb/IIIa binding inhibitory activities of 2,3-dihydro-1,4-benzodioxine derivatives through regio- and stereoisomerism, Recommanded Product: (R)-Oxiran-2-ylmethanol, the publication is European Journal of Medicinal Chemistry (2013), 329-340, database is CAplus and MEDLINE.

Enantiomers of 2,3-dihydro-1,4-benzodioxine derivatives possessing both thrombin and fibrinogen GPIIb/IIIa binding inhibitory activities were prepared from (R)- and (S)-glycidol as potential dual antithrombotic compounds The influence of chirality and substitution pattern on thrombin inhibition and on inhibition of fibrinogen binding to GPIIb/IIIa was analyzed. Docking studies were used in an attempt to rationalize the results. The (S)-isomers of both 2,3-dihydro-1,4-benzodioxine regioisomers at positions 6 and 7 were found to be better thrombin inhibitors than the corresponding (R)-enantiomers, whereas we observed that stereochem. does not display a consistent influence on fibrinogen GPIIb/IIIa binding inhibitory activity. Compound 11b, the (S)-isomer of the 6-substituted regioisomer, possessed the best balanced dual activity, with K_i(thrombin) = 1.67 ± 0.27 μM and IC_{50(GPIIb/IIIa)} = 0.665 ± 0.26 μM, raising the hope that merging anticoagulant and platelet antiaggregatory activities in the same mol. could lead to successful multitarget antithrombotic agents.

European Journal of Medicinal Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Recommanded Product: (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Wakamiya, Yuma published the artcileTotal Synthesis of Amphidinol 3: A General Strategy for Synthesizing Amphidinol Analogues and Structure-Activity Relationship Study, Recommanded Product: (R)-Oxiran-2-ylmethanol, the publication is Journal of the American Chemical Society (2020), 142(7), 3472-3478, database is CAplus and MEDLINE.

Amphidinol 3 (AM3) is a potent antifungal produced by the dinoflagellate Amphidinium klebsii. It was difficult to determine the absolute configuration of AM3 by using the scarce natural product due to the presence of numerous stereogenic centers on the acyclic carbon chain. Since the absolute configuration was partially determined on the basis of insufficient evidence, the originally proposed structure has been revised three times. Although recent progress on structure determination by computational anal. is remarkable, total synthesis is still the most reliable way to confirm structures. The first total synthesis of AM3 was achieved via expeditious assembly of three components in five steps, confirming the revised structure of AM3 after more than 20 years since its first discovery. The established synthetic route would be a general strategy for synthesizing amphidinol congeners. An artificial and simplified analog of AM3, which elicited antifungal activity comparable to that of AM3, was designed and synthesized. This is the first example of a biol. active artificial analog possessing a shorter polyol moiety, providing insight on the antifungal mode-of-action.

Journal of the American Chemical Society published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C23H43NP2, Recommanded Product: (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Alder, Kurt published the artcileSubstituting additions. IX. Substituting addition and diene synthesis with methylenecyclobutane, Safety of 1-Methylcyclobutan-1-ol, the publication is Chemische Berichte (1952), 556-65, database is CAplus.

cf. C.A. 44, 2927i. The substituting addition of maleic anhydride (I) to methylenecyclobutane (II), which is similar to the addition of I to methylenecyclohexane and -pentane, is studied. Heating an intimate mixture of 400 g. pentaerythrityl tetrabromide and 410 g. Zn dust in 600 cc. H₂O slowly to 85° with stirring and adding over a period of 2 hrs. 300 cc. MeOH in small portions give 70-85% II, b. 41-2°. Heating 25 cc. II and 50 g. I in 50 cc. dry C₆H₆ in a bomb tube 30 hrs. at 190-5°, washing the reaction product with Me₂CO into a beaker, and allowing the solvent to evaporate cause the crystallization of 35% adduct (III), consisting of 1 mol. II and 2 mols. I, m. 170-1°, which, on standing in the open air, changes to a tetracarboxylic acid (IV), m. 165-6°. On catalytic hydrogenation of 1 g. IV in AcOEt with PtO₂, the saturated tetracarboxylic acid, m. 193°, is formed. Heating 1.5 g. III and 1.4 g. S 2.5 hrs. at 240-5°, dissolving the reaction products in Na₂CO₃, oxidizing with KMnO₄, destroying the excess KMnO₄ with NaHSO₃, washing with ether, acidifying, evaporating the filtered solution in vacuo to dryness, and extracting the residue with hot Me₂CO give a tetracarboxylic acid (V) of Va as an oil. Oxidation of V with concentrated HNO₃ on a water bath and, finally, in a bomb tube at 165° gives trimellitic acid (VI), m. 221°, which, heated above its m.p. and sublimed, gives the anhydride, m. 161°. Distilling the residue of the mother liquor of III in vacuo gives 3 g. of a fraction, b₁₃ 155-60°, which, dissolved in Na₂CO₃, filtered, acidified, and extracted with ether, gives the dicarboxylic acid (VII), of VIIa, an adduct of 1 mol. isoprene and 1 mol. I, m. 155°. When hydrogenated in AcOEt in the presence of PtO₂, VII gives 4-methylcyclohexane-1,2-dicarboxylic acid, m. 165°. Heating 1 g. VII with 0.35 g. S 2.5 hrs. at 230-5° and then heating the reaction product with concentrated HNO₃, finally 6 hrs. in a bomb tube at 160°, give VI. The formation of VII is the result of a rearrangement of II via CH₂.CH₂.CH:CMe to CH₂:CHCMe:CH₂. Heating 20 cc. II and 35 cc. freshly distilled CH₂:CHCO₂H in 40 cc. dry C₆H₆ 30 hrs. at 200° and fractionally distilling in vacuo the reaction product from 2 runs give 45% distillate (VIII), b₁₃ 120-45°. Shaking VIII with ether and dilute KOH, acidifying the alk. solution with HCl, and extracting with ether give 18 g. of an acid mixture which, redistilled, b₁₃ 130-8°. It is separated into 7.2 g. crystalline 4-methyl-Δ³-tetrahydrobenzoic acid (IX), m. 100° (anilide, prepared via its Me ester, long needles, m. 154°; hydrazide, long silky nedles, m. 151-2°), and 7.9 g. of an oily adduct (X), CH₂.CMe:CH.CH₂.CH₂.CHCO₂H. Hydrogenating IX with PtO₂ in AcOEt and treating the Me ester, prepared with CH₂N₂, with PhNH₂ give the anilide of the saturated acid, C₁₄H₁₉ON, long needles, m. 130-1°. Ozonization of 2.5 g. IX in 100 cc. AcOEt with O containing 3-4% O₃ and reduction of the reaction product with PtO₂ and a few drops MeOH give MeCOCH₂CH₂CH(CO₂H)CH₂CO₂H, hard crystals, m. 122-3° (semicarbazone, m. 178°). Heating 1 g. IX with 4 cc. concentrated H₂SO₄ 15 min. on a boiling water bath and pouring the mixture on ice give p-MeC₆H₄CO₂H, m. 178°, in good yield. Heating 1.4 g. IX 2.5 hrs. at 230-5° with 0.64 g. S, dissolving the reaction product in Na₂CO₃, treating it with KMnO₄, decolorizing with NaHSO₃, and acidifying give p-C₆H₄(CO₂H)₂ (di-Me ester, m. 140°). Heating 1.4 g. X 2.5 hrs. at 230-5° with 0.64 g. S gives m-MeC₆H₄CO₂H, m. 110°, which, oxidized with KMnO₄, gives m-C₆H₄(CO₂H)₂ (di-Me ester m. 68°). Distillation of the residue of the washed ether solution obtained in the working up of VIII gives 10 g. 1-hydroxy-1-methylcyclobutane (XI) acrylate (XII), b₁₃ 125°, which (8 g.), refluxed 6 hrs. with concentrated KOH-MeOH, gives XI, b. 117-20° (phenylurethan m. 139°). Ozonization of XII gives HCHO. Acidification of the alk. solution gives 1.5 g. IX. Heating 20 cc. II and 20 cc. AcOH 48 hrs. at 200°, diluting the mixture with H₂O, and distilling the washed (dilute Na₂CO₃, H₂O) oil give 9 g. of a mixture, b. 140-200°. Saponification with KOH-MeOH of the fraction, b. 130-60°, gives XI. Refluxing 4 g. of the fraction, b. 170-85°, 4 hrs. with 2 g. I in a little ether, distilling off the ether and unreacted reagents, and dissolving the residue in hot concentrated Na₂CO₂H give the Na salt of an adduct of I with α-terpinene, as fatty shiny scales. Heating the free acid above its m.p. gives the anhydride, m. 62-3°.

Chemische Berichte published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Safety of 1-Methylcyclobutan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Dem’yanov, I. N. published the artcileVinyltrimethylene and its Derivatives, Category: alcohols-buliding-blocks, the publication is Zhurnal Russkago Fiziko-Khimicheskago Obshchestva (1913), 176-84, database is CAplus.

The alc. (a) obtained by shaking vinyltrimethylene (b) with H₂SO₄ (Gustavson, J. prakt. Chem., [2] 54, 104), not being oxidizable to an aldehyde or ketone, is doubtless tertiary; it b₇₅₅, 117.5-8.5° m. -5°, d₄²² 0.889, n₄²² 1.4315. Of the 2 formulas of (a), and preference is given to the 2nd. By converting (a) into an iodide (b₂₂ 50°) and treating the latter with Zn + AcOH a mixture of a hydrocarbon C₅H₁₀ (c) and the acetate of (a) was obtained. (c) b₇₅₃ 34-5°, d₀⁰ 0.6973, d₄⁰ 0.6805, n_D¹⁷ 1.3814; its formula is supposed to be. A hydrocarbon almost identical with (c) is more readily obtainable by reducing (b) with H + Pt black. The acetate of (c) b. 130-2.5°, d₄²⁰ 0.9351, n_D²⁰ 1.419.

Zhurnal Russkago Fiziko-Khimicheskago Obshchestva published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Wang, Bang-Jin published the artcileAn enantioselective potentiometric sensor for 2-amino-1-butanol based on chiral porous organic cage CC3-R, Related Products of alcohols-buliding-blocks, the publication is Molecules (2019), 24(3), 420/1-420/9, database is CAplus and MEDLINE.

Porous organic cages (POCs) have attracted extensive attention due to their unique structures and tremendous application potential in numerous areas. In this study, an enantioselective potentiometric sensor composed of a polyvinyl chloride (PVC) membrane electrode modified with CC3-R POC material was used for the recognition of enantiomers of 2-amino-1-butanol. After optimization, the developed sensor exhibited enantioselectivity toward S-2-amino-1-butanol (log KPotS,R = -0.98) with acceptable sensitivity, and a near-Nernstian response of 25.8 ± 0.3 mV/decade within a pH range of 6.0-9.0.

Molecules published new progress about 96-20-8. 96-20-8 belongs to alcohols-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Alcohol, name is 2-Aminobutan-1-ol, and the molecular formula is C9H22OSi, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Gu, Yu-Rui published the artcileIminyl Radical-Triggered Intermolecular Distal C(sp³)-H Heteroarylation via 1,5-Hydrogen-Atom Transfer (HAT) Cascade, HPLC of Formula: 20117-47-9, the publication is Organic Letters (2019), 21(4), 917-920, database is CAplus and MEDLINE.

An efficient iron-catalyzed intermol. remote C(sp³)-H heteroarylation of alkyl ketones has been developed via an iminyl radical-triggered 1,5-hydrogen-atom transfer (HAT) cascade. This protocol was amenable to a wide variety of alkyl ketones and heteroaryls, thus providing a straightforward method for the late-stage functionalization of alkylketones and heteroaryls to obtain, e.g., I.

Organic Letters published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C5H10O, HPLC of Formula: 20117-47-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Tomer, K. B. published the artcileMass spectrometry in structural and stereochemical problems. CCXXXI. Differentiation between tautomeric ion structures (phenol versus cyclohexadienone), Synthetic Route of 20117-47-9, the publication is Tetrahedron (1973), 29(22), 3491-6, database is CAplus.

Ion cyclotron resonance and pulsed double resonance spectra of ion-mol. reactions of bicyclo[2.2.2]oct-2-en-5,7-dione, PhOD, and C6D5OH with Pr2CO and 1-methylcyclobutanol were determined and the results applied to the structure determination of the C6H6O+ ion generated by electron impact induced expulsion of CH2:CO from PhOAc. The ion was PhO+, not cyclohexadienone+.

Tetrahedron published new progress about 20117-47-9. 20117-47-9 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic cyclic hydrocarbon,Alcohol, name is 1-Methylcyclobutan-1-ol, and the molecular formula is C4H8F3NO, Synthetic Route of 20117-47-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts